10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile

• ChemBase ID: 1385
• Molecular Formular: C21H23N3OS
• Molecular Mass: 365.49182
• Monoisotopic Mass: 365.15618337
• SMILES: S1c2c(N(CCCN3CCC(O)CC3)c3c1cccc3)cc(cc2)C#N
• Canonical SMILES: N#Cc1ccc2c(c1)N(CCCN1CCC(CC1)O)c1c(S2)cccc1
• InChI: InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2
• InChIKey: LUALIOATIOESLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile
• IUPAC Traditional name: propericiazine
• Brand Name: Neuleptil; Yaz
• Synonyms: Pericyazine; Pericyazine; Propericiazine; 10-[3-(4-Hydroxy-1-piperidinyl)propyl]-10H-phenothiazine-2-carbonitrile; 2-Cyano-10-[3-(4-hydroxypiperidino)propyl]phenothiazine; Aolept; Bayer 1409; FI 6145; Nelactil; Nemactil; Neulactil; Neuleptil; Periciazine; Periciazinum; Properciazine; Propericiazine; Propericyazine; RP 8909; SKF 20716

Database IDs

• CAS Number: 2622-26-6
• PubChem SID: 160964845; 46505085
• PubChem CID: 4747
• ATC CODE: N05AC01
• KEGG ID: D01485
• Unique Ingredient Identifier: 3405M6FD73
• Wikipedia Title: Pericyazine

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.179289
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.32233855
• LogD (pH = 7.4): 2.0884066
• Log P: 3.1051114
• Molar Refractivity: 108.3974 cm^3
• Polarizability: 41.353477 Å^3
• Polar Surface Area: 50.5 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.78
• LOG S: -3.79
• Solubility (Water): 5.90e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.038 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 3.52 [HANSCH,C ET AL. (1995)]

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: POM (UK)

DETAILS

DrugBank - DB01608

• Drug Groups: approved
• Description: Propericiazine is a phenothiazine of the piperidine group. It has been shown to reduce pathologic arousal and affective tension in some psychotic patients, while the symptoms of abnormal mental integration are relatively unaffected. It is a sedative phenothiazine with weak antipsychotic properties. It also has adrenolytic, anticholinergic, metabolic and endocrine effects and an action on the extrapyramidal system. It is used as an adjunctive medication in some psychotic patients, for the control of residual prevailing hostility, impulsiveness and aggressiveness. Pericyazine, like other phenothiazines, is presumed to act principally in the subcortical areas, by producing what has been described as a central adrenergic blockade.
• Indication: For use as adjunctive medication in some psychotic patients. Propericiazine (Pericyazine)is used for the control of residual prevailing hostility, impulsiveness and aggressiveness.
• Pharmacology: Pericyazine is a phenothiazine of the piperidine group. It has been shown to reduce pathologic arousal and affective tension in some psychotic patients, while the symptoms of abnormal mental integration are relatively unaffected. It is a sedative phenothiazine with weak antipsychotic properties. It also has adrenolytic, anticholinergic, metabolic and endocrine effects, and an action on the extrapyramidal system.
• Toxicity: In milder cases of phenothiazine overdosage the patient may be agitated, delirious and confused. Frequently he is lethargic or in a comatose state. Twitching, dystonic movements or convulsions may be present and hypotension, cardiovascular collapse, arrhythmias and hypothermia might be observed.
• Affected Organisms: Humans and other mammals

Toronto Research Chemicals - P287360

Psychotherapeutic phenothiazine. Antipsychotic.

REFERENCES

• Schafer, et al.: Toxicol. Appl. Pharmacol., 21, 315 (1972)
• Kaye, J., et al.: Br. J. Clin. Pharmacol., 56, 569 (1972)
• Tschoner, A., et al.: Pharmacopsychiatry, 42, 29 (1972)